Thermal decomposition of allantoin as probed by matrix isolation FTIR spectroscopy

Tetrahedron

Volumn 65, Issue 47, 2009, Pages 9719-9727

  Kus N ^a,b   Bayari, S Haman ^c   Fausto, R ^b  

^a ANADOLU UNIVERSITY   (Turkey)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c HACETTEPE UNIVERSITY   (Turkey)

Author keywords

Allantoin; Conformational analysis; DFT calculations; Low temperature matrix isolation and room temperature crystalline state IR spectra; Thermal decomposition

Indexed keywords

ALLANTOIN; AMMONIA; ARGON; CARBON; ISOCYANATE; UREA;

ARTICLE; DECOMPOSITION; DENSITY FUNCTIONAL THEORY; GAS ANALYSIS; HYDROGEN BOND; INFRARED SPECTROSCOPY; ISOMERIZATION; METHODOLOGY; MOLECULE; PRIORITY JOURNAL; ROOM TEMPERATURE; SOLID STATE; THERMAL ANALYSIS;

EID: 70349974564     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.088     Document Type: Article

References (53)

1. Mendel L.B., and Dankin H.D. J. Biol. Chem. (1910) 153
2. Christman A.A. J. Biol. Chem. (1926) 173
3. Robinson W. J. Parasitol. 21 (1935) 354
4. Shestopalov A.V., Shkurat T.P., Mikashinovich Z.I., Kryzhanovskaia I.O., Bogacheva M.A., Lomteva S.V., Prokof'ev V.P., and Gus'kov E.P. Izv. Akad. Nauk.: Ser. Biol. 5 (2006) 541
5. Simoyi M.F., Falkenstein E., Van Dyke K., Blemings K.P., and Klandorf H. Comp. Biochem. Physiol. B: Biochem. Mol. Biol. 135 (2003) 325
6. Fujihara S., and Yamaguchi M. Phytochemistry 17 (1978) 1239
7. Young K.G., Wentworth H.P., and Hawkins W.W. J. Pharmacol. Exp. Ther. 81 (1944) 1
8. Fujiwara S., and Noguchi T. Biochem. J. 312 (1995) 315
9. Thornfeldt C. Dermat. Surg. 31 (2005) 873
10. Disalvo R.M. Chem. Manufact. Cosmetics 3 (2002) 29
11. Eggensperger H. Multiaktive Wirkstoffe für Kosmetika (1995) 9
12. Stark G.R. Biochemistry 4 (1965) 2363
13. Stark G.R. Biochemistry 4 (1965) 1030
14. Haley R.J., and Ward D.M. Am. J. Kidney Dis. 8 (1986) 115
15. E Roxborough H., and Young I.S. Med. Hypotheses 45 (1995) 125
16. Gómez-Zavaglia A., Reva I.D., Frija L., Cristiano M.L., and Fausto R. J. Photochem. Photobiol. A: Chem. 179 (2006) 243
17. Caussé E., Pradelles A., Dirat B., Negre-Salvayre A., Salvayre R., and Couderc F. Electrophoresis 28 (2007) 381
18. Jin P., Ma J., Wu X., Zou D., Sun C., and Hu X. J. Pharm. Biomed. Anal. 50 (2009) 293
19. Kim K.M., Henderson G.N., Frye R.F., Galloway C.D., Brown N.J., Segal M.S., Imaram W., and Johnson R.J. J. Chromatogr., B 877 (2009) 65
20. Lagendijk J., Ubbink J.B., and Vermaak W.J. J. Chromatogr. Sci. 33 (1995) 186
21. Mootz D. Acta Crystallogr. 19 (1965) 726
22. Kahn K., and Tipton P.A. Bioorg. Chem. 27 (2000) 62
23. Kahn, K. Kinetic and Mechanistic Characterization of the Urate Oxidade reaction, Ph.D. Thesis, University of Missouri, Columbia, USA, 1998.
24. Sabbahm R., Wu A.X., Chickos J.S., Leitão M.L.P., Roux N.V., and Torres L.A. Thermochim. Acta 331 (1995) 93
25. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., González C., and Pople J.A. GAUSSIAN 03 Revision B. 04 (2003), Gaussian, Pittsburgh, PA
26. McLean A.D., and Chandler G.S. J. Chem. Phys. 72 (1980) 5639
27. Krishnan R., Binkley J.S., Seeger R., and Pople J.A. J. Chem. Phys. 72 (1980) 650
28. Becke A.D. Phys. Rev. A 38 (1988) 3098
29. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
30. Vosko S.H., Wilk L., and Nusair M. Can. J. Phys. 58 (1980) 1200
31. Frisch M.J., Head-Gordon M., and Pople J.A. Chem. Phys. Lett. 166 (1990) 281
32. Csaszar P., and Pulay P. J. Mol. Struct. 114 (1984) 31
33. Peng C., and Schlegel H. Isr. J. Chem. 33 (1994) 449
34. Schachtschneider J.H., and Mortimer F.S. Vibrational Analysis of Polyatomic Molecules. VI FORTRAN IV Programs for Solving the Vibrational Secular Equation and for the Least-Squares Refinement of Force Constants, Project No. 31450. Structural Interpretation of Spectra (1965), Shell Development, Houston, TX
35. Reva I.D., Stepanian S.G., Adamowicz L., and Fausto R. Chem. Phys. Lett. 374 (2003) 631
36. Lopes Jesus A.J., Rosado M.T.S., Reva I., Fausto R., Eusébio M.E.S., and Redinha J.S. J. Phys. Chem. A 112 (2008) 4669
37. Rosado M.T.S., Lopes Jesus A.J., Reva I.D., Fausto R., and Redinha J.S. J. Phys. Chem. A 113 (2009) 7499
38. Dobrowolski J.C., Kolos R., Sadlej J., and Mazurek A.P. Vib. Spectrosc. 29 (2002) 261
39. Ware E. Chem. Rev. 46 (1950) 403
40. Schaber P.M., Colson J., Higgins S., Thielen D., Anspach B., and Brauer J. Thermochim. Acta 424 (2004) 131
41. Tokmakov I.V., Alavi S., and Thompson D.L. J. Phys. Chem. A 110 (2006) 2759
42. Bohn R.B., and Andrews L. J. Phys. Chem. 93 (1989) 3974
43. Bossa J.B., Duvernay F., Theulé P., Borget F., and Chiavassa T. Chem. Phys. 354 (2008) 211
44. Lundell J., Krajewska M., and Räsänen M. J. Phys. Chem. A 102 (1998) 6643
45. Teles J.H., Maier G., Hess Jr. B.A., Schaad L.J., Winnewesser M., and Winnewisser B.P. Chem. Ber. 122 (1989) 753
46. Coffey M.J., Berghout H.L., Woods III E., and Crim F.F. J. Chem. Phys. 110 (1999) 10850
47. McLean A.D., Loew G.H., and Berkowitz D.S. J. Mol. Spectrosc. 64 (1977) 184
48. Cugley P.A., and Pullin A.D.E. Chem. Phys. Lett. 19 (1973) 203
49. Stewart J.E. J. Chem. Phys. 26 (1957) 248
50. Rozenberg M., Shoham G., Reva I.D., and Fausto R. Spectrochim. Acta A 60 (2004) 2319
51. Rozenberg M., Shoham G., Reva I.D., and Fausto R. Spectrochim. Acta A 60 (2004) 463
52. Rozenberg M., Shoham G., Reva I.D., and Fausto R. Spectrochim. Acta A 59 (2003) 3253
53. Rozenberg M., Shoham G., Reva I.D., and Fausto R. Phys. Chem. Chem. Phys. 7 (2005) 2376